Using an extended case vignette, the author explores addiction, specifically compulsive gambling and substance abuse, from several psychoanalytic perspectives. Addiction/compulsive behavior is explained as a strategy for managing loss at key developmental stages. The concept of trauma repetition is utilized to understand both the repetitious nature of chronic addiction, and the trauma that underlies it. The process of recovery is chronicled through the therapeutic relationship. A classic children's story is referred to as it threads through the narrative.